Synthesis and SAR studies of pyrazole-3-carboxamides and -3-carbonyl thioureides including chiral moiety: Novel candidates as antibacterial agents

Ishak Bildirici, Adnan Cetin, Nurettin Menges, Yusuf Alan

Abstract


A series of tetrasubstituted pyrazole-3-carboxamides (3a–c) and pyr­azole-3-carbonyl thioureides (6ac) were synthesized and their structures char­ac­terized by IR, NMR and elemental analysis. The antibacterial potential against specific Gram-positive and Gram-negative strains and the antifungal activities of all novel compounds were investigated. Structure–activity relation­ships (SAR) studies and some theoretical parameters (ClogP, CMR, PSA and ESP) of the compounds were performed on these two pyrazole derivatives. Pyrazole-3-carboxylate ester 2 was used for the synthesis of the carboxamide derivatives. The reactions of pyrazole-3-carbonyl isothiocyanate 5 with appro­priate chiral amino alco­hols were utilized for synthesizing the thioureide deri­vatives. Both of these types of pyrazole derivatives including a chiral moiety exhibited pronounced antibacterial activities. According to the present in vitro study, some of the pro­mising compounds might be new candidates for a new generation of antibacterial drugs.

Keywords


biological activity; chiral amino alcohols; pyrazole; heterocyclic compounds

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DOI: https://doi.org/10.2298/JSC170313029B

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